Dialkyl esters of long-chain alkylphosphonates



Patented Feb. 17,1948

UNITED STATES PATENT OFFICE DIALKYEESTERS F LONG-CHAIN ALKYLPHOSPHONATES Max '1. Goehel, Rocky River, Ohio, assignor to E.'I. du Pont de Nemours & Company, Wilmington, Del., a corporation of Delaware No Drawing. Application March I, 1946,

Serial N0. 652,788

1 Claim. (01. ace-461) This invention relates to new compositions of matter containing phosphorus. More particular ly this invention relates to dialkyl esters of lon chain alkyl-phosphonates and methods for their preparation.

An object of this invention is to provide new compositions of matter. A further object is to provide novel dialkyl esters of long-chain alkylphosphonates and methods for their preparation.

These objects are accomplished by preparing new dialkyl esters oi long-chain alkylphosphonates having the formula:

0 1 01V i where R is a normal alkyl, 1. e., saturated straight-chain aliphatic hydrocarbon radical of eight to eighteen carbon atoms and R is a lower alkyl radical of one to four carbon atoms.

The compounds of this invention can be pre- 2 tri-methyl phosphite, tri-propyl phosphite and tri-butyl phosphite.

In addition to the diethyl dodecylphosphonate of the example other dialkyl esters of saturated long-chain alkylphosphonates are diethyl decylto be understood that I do not limit myself to pared by' reacting a long-chain (eight-eighteen Y carbon atoms) n-alkyl chloride with a lower triaikyl phosphite under conditions of elevated temperature and under superatmospheric pressure. 'tli'he product is then isolated by vacuum distilla- This invention is further illustrated by the i'ollowing example. in which parts are by welsht, unless otherwise specified.

Example as phonate.

a mixture of 46.4 parts of trlethyl phosphlte and 68.0 parts of dodecyl chloride (laurylchloride) were heated in a sealed reaction vessel at 210 C. for 8 hours. The reaction mixture was then subfeeted to vacuum distillation and 20.5 parts of dlethyl dodecylphosphonate boiling at 164-165.

C./1.2 mm. was obtained. This product had a refractive index of 1.4389 at C.

Analysis: Calculated for CmHatOaP: C, 62.60; H,

11.45. Found: C, 62.13:H. 11.74.

Qther saturated n-alkyl halides which are useful in forming the compounds oi this "invention are n-octyl chloride, n-decyl chloride, n-tetradecyl chloride. n-hexadecyl chloride, n-octadecyl chloride. The bromides and iodides can also be Other trlalkyl phcsbhites which can be used In preparing the compolmds of-this invention are the specific embodiments thereof except as defined in the appended claim.

I claim: The chemical compound diethyl dodecylphosmax '1'. GOEBEL.

REFERENCES CITED The following references are of record in the die of this patent:

UNITED STATES PATENTS Number Name Date 2,365,466 Hamilton D80. 19, 1944 2,397,422 KOS018 .D0fl Mar. 26, 1948 OTHER REFERENCES Beilstein, "Handbuch der Org. Chem.," 4th ed., vol .IV. page 596.

Beilstein, "Handbuch der Org. Chem.," 4th ed., supplemental vol. III/IV, page 573.

Arbuzov, Chem. Abstracts," vol. 25, page 2414 (1931).

Chemical Industries, vol. 55, P ge 581 (Oct.

Kosolapofl, -"Jour. Am. Chem. 800.," vol. 66, pages 109-111 (1944). g

Kosolapofl, "Jour. Am. Chem. 800.," vol. 6'7. pages 1180 to 1182, 2259 to 2260 (1945). 

